This reaction is followed by bromination and rearrangement steps to generate flavonols in the Auwers synthesis. Proline catalyzes an asymmetric version of this reaction used to generate Hajos-Parrish (“high-OHSH-pare-ish”) ketones for steroid synthesis. This reaction forms citrate from oxalo·acetate and acetyl-CoA in the first step of the TCA cycle. This reaction’s chair-like intermediate determines its stereochemistry according to the (*) Zimmerman-Traxler model. This reaction follows a Michael addition in the mechanism for the Robinson Annulation. Under basic conditions, this reaction’s final step occurs via an E1cB mechanism to form an alpha-beta unsaturated product. For 10 points, name this reaction where an enolate attacks a carbonyl to make a product with both aldehyde and alcohol groups. ■END■
ANSWER: aldol condensation [or aldol reaction; or aldol addition]
<Munir Siddiqui, Chemistry>
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